Novel chrysene derivatives and organic electrical device using the same

ABSTRACT

The present invention relates to a novel chrysene derivative and an organic electronic device using the same. A chrysene according to the present invention may act as a hole injection, hole transport, electron injection and transport, or light emitting material in an organic light emitting device and an organic electronic device, and in particular, may be used alone as a light emitting host or a dopant.

TECHNICAL FIELD

The present invention relates to a novel chrysene derivative and anorganic electronic device using the same. This application claimspriority from Korean Patent Application No. 10-2008-0114661 filed onNov. 18, 2008 in the KIPO, the disclosure of which is incorporatedherein by reference in its entirety.

BACKGROUND ART

An organic electronic device means a device that requires exchanging ofelectric charges between electrodes using holes and/or electrons andorganic materials. The organic electronic device may be largely dividedinto the following categories according to an operation principle.First, there is an electronic device in which an exciton is formed in anorganic layer by a photon that flows from an external light source tothe device, the exciton is separated into electrons and holes, and theelectrons and the holes are transferred to the other electrodes and usedas a current source (voltage source). Second, there is an electronicdevice in which holes and/or electrons are injected into an organicmaterial semiconductor forming an interface in respects to the electrodeby applying a voltage or a current to two or more electrodes, and thedevice is operated by the injected electrons and holes.

As examples of the organic electronic device, there are an organic lightemitting device, an organic solar cell, an organic photoconductor (OPC),an organic transistor and the like, and all of them require a holeinjection or transport material, an electron injection or transportmaterial or a light emitting material in order to drive the device.

Hereinafter, an organic light emitting device will be mainly describedin detail. However, in the organic electronic devices, all of the holeinjection or transport material, an electron injection or transportmaterial or a light emitting material are operated on the basis of thesimilar principle.

In general, an organic light emitting phenomenon means a phenomenon thatconverts electric energy into light energy by using an organic material.The organic light emitting device using the organic light emittingphenomenon has a structure which generally comprises an anode, acathode, and an organic layer that is disposed between them. Herein,most organic layers have a multilayered structure that comprisesdifferent materials in order to increase efficiency and stability of theorganic light emitting device, and for example, it may comprise a holeinjection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer and the like. Inthe organic light emitting device structure, if a voltage is appliedbetween two electrodes, holes are injected from an anode and electronsare injected from a cathode to the organic material layer, and when theinjected holes and the electrons meet each other, an exciton is formed,and light is emitted when the exciton falls to a bottom state. It isknown that this organic light emitting device has properties such asmagnetic light emission, high brightness, high efficiency, low drivingvoltage, a wide viewing angle, high contrast, high speed response andthe like.

In the organic light emitting device, the material that is used in theorganic material layer may be classified into a light emitting materialand an electric charge material, for example, a hole injection material,a hole transport material, an electron transport material, an electroninjection material according to a function thereof. The light emittingmaterial may be classified into a high molecule type and a low moleculetype according to the molecular weight, and a fluorescent material and aphosphorescent material according to a mechanism of light emission. Inaddition, the light emitting material may be classified into blue,green, and red light emitting materials and yellow and orange lightemitting materials in order to realize better natural colors accordingto the emission color.

Meanwhile, in the case of when only one material is used as a lightemitting material, by interaction between molecules, there are problemsin that the maximum light emitting wavelength moves to the longwavelength, the color purity is lowered, or efficiency of the device islowered because of reduced effect of light emission. Therefore, in orderto increase color purity and increase emission efficiency throughtransferring of energy, a host/dopant system may be used as the lightemitting material. The principle is that if a small amount of dopantthat has a smaller energy band gap than a host forming the lightemitting layer is mixed with the light emitting layer, the exciton thatis generated from the light emitting layer is transported to the dopantto emit light at high efficiency. At this time, since the wavelength ofthe host is moved to the wavelength bandwidth of the dopant, a desiredwavelength of light may be obtained according to the kind of dopant.

In order to sufficiently show excellent properties of the above organiclight emitting device, a material constituting the organic materiallayer in the device, for example, the hole injection material, the holetransport material, the light emitting material, the electron transportmaterial, the electron injection material and the like should besupported by stable and efficient materials. However, the development ofa stable and efficient organic material layer material for organic lightemitting devices has not yet been made. Therefore, there is a demand fordeveloping a novel material, and the demand for developing the novelmaterial is similarly applied to the other organic electronic device.

DISCLOSURE Technical Problem

The present invention has been made to solve the above problems in therelated art, and it is an object of the present invention to provide anovel stable and efficient chrysene derivative and an organic electronicdevice using the same.

Technical Solution

In order to solve the above object, an aspect of the present inventionprovides a compound that is represented by the following Formula 1.

wherein

R1 is selected from the group consisting of substituted or unsubstitutedC₁˜C₄₀ alkyl group; substituted or unsubstituted C₃˜C₄₀ cycloalkylgroup; substituted or unsubstituted C₂˜C₄₀ heterocycloalkyl group;substituted or unsubstituted C₂˜C₄₀ alkenyl group; substituted orunsubstituted C₁˜C₄₀ alkoxy group; substituted or unsubstituted aminogroup; substituted or unsubstituted C₆˜C₄₀ aryl group; substituted orunsubstituted C₃˜C₄₀ heteroaryl group that comprises O, N, or S as aheteroatom; and substituted or unsubstituted C₃˜C₄₀ heteroarylaminegroup that comprises O, N, or S as a heteroatom,

R2 is selected from the group consisting of substituted or unsubstitutedC₁˜C₄₀ alkyl group; substituted or unsubstituted C₃˜C₄₀ cycloalkylgroup; substituted or unsubstituted C₃˜C₄₀ heterocycloalkyl group;substituted or unsubstituted C₂˜C₄₀ alkenyl group; substituted orunsubstituted C₁˜C₄₀ alkoxy group; substituted or unsubstituted aminogroup; substituted or unsubstituted C₆˜C₄₀ aryl group; substituted orunsubstituted C₃˜C₄₀ heteroaryl group that comprises O, N, or S as aheteroatom; substituted or unsubstituted C₅˜C₄₀ arylamine group; andsubstituted or unsubstituted C₃˜C₄₀ heteroarylamine group that comprisesO, N, or S as a heteroatom,

R3 to R7 are each independently selected from the group consisting ofhydrogen; substituted or unsubstituted C₁˜C₄₀ alkyl group; substitutedor unsubstituted C₃˜C₄₀ cycloalkyl group; substituted or unsubstitutedC₂˜C₄₀ heterocycloalkyl group that comprises O, N, or S as a heteroatom;substituted or unsubstituted C₂˜C₄₀ alkenyl group; substituted orunsubstituted C₁˜C₄₀ alkoxy group; substituted or unsubstituted aminogroup; substituted or unsubstituted C₆˜C₄₀ aryl group; substituted orunsubstituted C₃˜C₄₀ heteroaryl group that comprises O, N, or S as aheteroatom; substituted or unsubstituted C₅˜C₄₀ arylamine group; andsubstituted or unsubstituted C₃˜C₄₀ heteroarylamine group that comprisesO, N, or S as a heteroatom, and may form an aliphatic, aromatic,heteroaliphatic or heteroaromatic condensate ring or a spiro bond inconjunction with an adjacent group,

X is selected from the group consisting of hydrogen; substituted orunsubstituted C₁˜C₄₀ alkyl group; substituted or unsubstituted C₃˜C₄₀cycloalkyl group; substituted or unsubstituted C₂˜C₄₀ heterocycloalkylgroup that comprises O, N, or S as a heteroatom; substituted orunsubstituted C₂˜C₄₀ alkenyl group; substituted or unsubstituted C₁˜C₄₀alkoxy group; substituted or unsubstituted amino group; substituted orunsubstituted C₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀heteroaryl group that comprises O, N, or S as a heteroatom; andsubstituted or unsubstituted C₃˜C₄₀ heteroarylamine group that comprisesO, N, or S as a heteroatom, and may form an aliphatic, aromatic,heteroaliphatic or heteroaromatic condensate ring or a spiro bond inconjunction with an adjacent group, and

all of R3 to R7, and X are not hydrogen

In order to accomplish the above object, a second aspect of the presentinvention provides an organic electronic device which comprises a firstelectrode, a second electrode, and one or more organic material layersthat are disposed between the first electrode and the second electrode,wherein one or more layers of the organic material layers comprise thecompound that is represented by Formula 1.

Advantageous Effects

A compound according to the present invention may act as a holeinjection, hole transport, electron injection and transport, or lightemitting material in an organic light emitting device and an organicelectronic device, and the organic electronic device according to thepresent invention shows excellent properties in terms of efficiency, adriving voltage, and stability.

DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view that illustrates a structure of an organiclight emitting device according to an embodiment of the presentinvention; and

FIG. 2 is a graph that illustrates an excitation wavelength and a lightemission wavelength of the film (200A) of a compound 1-18.

BEST MODE

Hereinafter, the present invention will be described in more detail.

An aspect of the present invention relates to a compound that isrepresented by Formula 1.

The substituent group of Formula 1 will be described in detail below.

In R2 to R7, in the case of when alkyl group, cycloalkyl group,heterocycloalkyl group, alkenyl group, alkoxy group, amino group, arylgroup, heteroaryl group, arylamine group and heteroarylamine group aresubstituted by the other functional group, they are substituted by oneor more groups that are selected from the group consisting of halogen,deuterium, amino group, nitrile group, nitro group, C₁˜C₄₀ alkyl group,C₂˜C₄₀ alkenyl group, C₁˜C₄₀ alkoxy group, C₃˜C₄₀ cycloalkyl group,C₂˜C₄₀ heterocycloalkyl group that comprises O, N or S as a heteroatom,C₆˜C₄₀ aryl group and C₃˜C₄₀ heteroaryl group that comprises O, N or Sas a heteroatom,

in R1 and X, in the case of when alkyl group, cycloalkyl group,heterocycloalkyl group, alkenyl group, alkoxy group, amino group, arylgroup, heteroaryl group and heteroarylamine group are substituted by theother functional group, they are substituted by one or more groups thatare selected from the group consisting of halogen, deuterium, nitrilegroup, nitro group, C₁˜C₄₀ alkyl group, C₂˜C₄₀ alkenyl group, C₁˜C₄₀alkoxy group, C₃˜C₄₀ cycloalkyl group, C₂˜C₄₀ heterocycloalkyl groupthat comprises O, N or S as a heteroatom, C₆˜C₄₀ aryl group and C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom.

In the case of when there is no specific description in Formula 1, thealkyl group and alkoxy group have preferably 1 to 40 carbon atoms andmore preferably 1 to 20 carbon atoms. In addition, the alkenyl group haspreferably 2 to 40 carbon atoms and more preferably 2 to 20 carbonatoms. In addition, the aryl group has preferably 6 to 40 carbon atomsand more preferably 6 to 20 carbon atoms. In addition, the heteroringgroup has preferably 4 to 40 carbon atoms and more preferably 4 to 20carbon atoms. In addition, the aryl amine group has preferably 6 to 60carbon atoms and more preferably 6 to 24 carbon atoms. In addition, theheteroarylamine group has preferably 4 to 60 carbon atoms and morepreferably 4 to 20 carbon atoms.

In the case of when there is no specific description in Formula 1, theterm “substituted or unsubstituted” means that it is substituted orunsubstituted by one or more substituent groups that are selected fromthe group consisting of halogen group, alkyl group, alkenyl group,alkoxy group, aryl group, arylalkyl group, arylalkenyl group, heteroringgroup, carbazolyl group, fluorenyl group, nitrile group and acetylenegroup, but they are not limited thereto.

In Formula 1, R1 is selected from the group consisting of substituted orunsubstituted C₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom; andsubstituted or unsubstituted C₃˜C₄₀ heteroarylamine group that comprisesO, N or S as a heteroatom,

R2 may be selected from the group consisting of substituted orunsubstituted C₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom; substitutedor unsubstituted C₅˜C₄₀ arylamine group; and substituted orunsubstituted C₃˜C₄₀ heteroarylamine group that comprises O, N or S as aheteroatom.

In addition, R1 is selected from the group consisting of C₆˜C₂₀ arylgroup; C₆˜C₄₀ aryl group or C₆˜C₂₀ aryl group that comprises O, N or Sas a heteroatom and substituted by C₃˜C₄₀ heteroaryl group; and C₃˜C₂₀heteroaryl group that is substituted by C₆˜C₂₀ aryl group and comprisesO, N or S as a heteroatom, and

R2 may be selected from the group consisting of C₆˜C₂₀ aryl group;C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom or C₅˜C₄₀arylamine group; C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀aryl group and comprises O, N or S as a heteroatom; and C₆˜C₂₀ arylaminegroup.

It is preferable that detailed examples of R1 are selected from thegroup consisting of substituent groups represented by the followingStructural Formulas, but they are not limited thereto.

It is preferable that detailed examples of R2 are selected from thegroup consisting of substituent groups represented by the followingStructural Formulas, but they are not limited thereto.

In Formula 1, R3 to R7 may be all hydrogen or four of R3 to R7 and X maybe hydrogen.

In the case of when R3 to R7 are all hydrogen, it is preferable that Xis selected from the group consisting of substituted or unsubstitutedC₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀ heteroaryl groupthat comprises O, N or S as a heteroatom; and substituted orunsubstituted C₃˜C₄₀ heteroarylamine group that comprises O, N or S as aheteroatom.

In addition, in the case of when R3 to R7 are all hydrogen, it is morepreferable that X is selected from the group consisting of C₆˜C₂₀ arylgroup; C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group, orC₃˜C₄₀ heteroaryl group that comprises O, N or S as a heteroatom; andC₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl group andcomprises O, N or S as a heteroatom.

It is preferable that detailed examples of X are selected from the groupconsisting of substituent groups represented by the following StructuralFormulas, but they are not limited thereto.

In the case of when four of R3 to R7 and X are hydrogen, it ispreferable that the substituent group except for hydrogen among R3 to R7is selected from the group consisting of substituted or unsubstitutedC₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀ heteroaryl groupthat comprises O, N or S as a heteroatom; substituted or unsubstitutedC₅˜C₄₀ arylamine group; and substituted or unsubstituted C₃˜C₄₀heteroarylamine group that comprises O, N or S as a heteroatom.

In addition, in the case of when four of R3 to R7 and X are hydrogen, itis more preferable that the substituent group except for hydrogen amongR3 to R7 is selected from the group consisting of C₆˜C₂₀ aryl group;C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom or C₅˜C₄₀arylamine group; C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀aryl group and comprises O, N or S as a heteroatom; and C₆˜C₂₀ arylaminegroup.

In the case of when four of R3 to R7 and X are hydrogen, it ispreferable that the substituent group except for hydrogen among R3 to R7is selected from the group consisting of the substituent groupsrepresented by the following Structural Formulas, but they are notlimited thereto.

In particular, in the compound according to the present invention, R1 isselected from the group consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ arylgroup that is substituted by C₆˜C₄₀ aryl group or C₃˜C₄₀ heteroarylgroup that comprises O, N or S as a heteroatom; and C₃˜C₂₀ heteroarylgroup that is substituted by C₆˜C₂₀ aryl group and comprises O, N or Sas a heteroatom; and R2 is selected from the group consisting of C₆˜C₂₀aryl group; C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group,C₃˜C₄₀ heteroaryl group that comprises O, N or S as a heteroatom orC₅˜C₄₀ arylamine group; C₃˜C₂₀ heteroaryl group that is substituted byC₆˜C₂₀ aryl group and comprises O, N or S as a heteroatom; and C₆˜C₂₀arylamine group; and

it is preferable that X and R7 that are symmetrical to R1 and R2 withthe center of the chrysene core are hydrogen, and at least one of R3 toR6 is selected from the group consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀aryl group that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀ heteroarylgroup that comprises O, N or S as a heteroatom or C₅˜C₄₀ arylaminegroup; C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl groupand comprises O, N or S as a heteroatom; and C₆˜C₂₀ arylamine group.

More preferably, R1 is selected from the group consisting of C₆˜C₂₀ arylgroup; C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group orC₃˜C₄₀ heteroaryl group that comprises O, N or S as a heteroatom; andC₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl group andcomprises O, N or S as a heteroatom; R2 is selected from the groupconsisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ aryl group that is substitutedby C₆˜C₄₀ aryl group, C₃˜C₄₀ heteroaryl group that comprises O, N or Sas a heteroatom or C₅˜C₄₀ arylamine group; C₃˜C₂₀ heteroaryl group thatis substituted by C₆˜C₂₀ aryl group and comprises O, N or S as aheteroatom; and C₆˜C₂₀ arylamine group;

R5 is selected from the group consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀aryl group that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀ heteroarylgroup that comprises O, N or S as a heteroatom or C₅˜C₄₀ arylaminegroup; C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl groupand comprises O, N or S as a heteroatom; and C₆˜C₂₀ arylamine group, and

R3, R4, R6, R7 and X are hydrogen, but they are not limited thereto.

As described above, the compound that is represented by Formula 1according to the present invention may be a compound that has at leastthree functional groups with the center of chrysene core by comprisingspecific functional group on at least one of R1 and R2, R3 to R7, and X.

In particular, in the compound according to the present invention, inthe case of when specific functional group is comprised in R1, R2, andR5 of Formula 1, the organic electronic device that comprises thecompound may show improved properties such as efficiency, drivingvoltage, and stability.

In the compound that is represented by Formula 1 according to thepresent invention, detailed examples of each substituent group aredescribed in the following Tables 1 to 6, but they are not limitedthereto.

TABLE 1 R3, R4, R6, Formula R1 R2 R5 X, R7 1-1 phenyl phenyl phenyl H1-2 phenyl phenyl

H 1-3 phenyl phenyl

H 1-4 phenyl phenyl

H 1-5 phenyl phenyl

H 1-6 phenyl phenyl

H 1-7 phenyl phenyl

H 1-8 phenyl phenyl

H 1-9 phenyl phenyl

H 1-10 phenyl phenyl

H 1-11 phenyl phenyl

H 1-12 phenyl phenyl

H 1-13 phenyl phenyl

H 1-14 phenyl phenyl

H 1-15 phenyl phenyl

H 1-16 phenyl phenyl

H 1-17 phenyl phenyl

H 1-18 phenyl phenyl

H 1-19 phenyl phenyl

H 1-20 phenyl phenyl

H 1-21 phenyl phenyl

H 1-22 phenyl phenyl

H 1-23 phenyl

phenyl H 1-24 phenyl

phenyl H 1-25 phenyl

phenyl H 1-26 phenyl

phenyl H 1-27 phenyl

phenyl H 1-28 phenyl

phenyl H 1-29 phenyl

phenyl H 1-30 phenyl

phenyl H 1-31 phenyl

phenyl H 1-32 phenyl

phenyl H 1-33 phenyl

phenyl H 1-34 phenyl

phenyl H 1-35 phenyl

phenyl H 1-36 phenyl

phenyl H 1-37 phenyl

phenyl H 1-38 phenyl

phenyl H 1-39 phenyl

phenyl H 1-40 phenyl

phenyl H 1-41 phenyl

phenyl H 1-42 phenyl

phenyl H 1-43 phenyl

phenyl H 1-44

phenyl

H 1-45

phenyl

H 1-46

phenyl

H 1-47

phenyl

H 1-48

phenyl

H 1-49

phenyl

H 1-50

phenyl

H 1-51

phenyl

H 1-52

phenyl

H 1-53

phenyl

H 1-54

phenyl

H 1-55

phenyl

H 1-56

phenyl

H 1-57

phenyl

H 1-58

phenyl

H 1-59

phenyl

H 1-60

phenyl

H 1-61

phenyl

H 1-62

phenyl

H 1-63

phenyl

H 1-64

phenyl

H 1-65

phenyl

H 1-66

phenyl

H 1-67

phenyl

H 1-68

phenyl

H 1-69

phenyl

H 1-70

phenyl

H 1-71

phenyl

H 1-72

phenyl

H 1-73

phenyl

H 1-74

phenyl

H 1-75

phenyl

H 1-76

phenyl

H 1-77

phenyl

H 1-78

phenyl

H 1-79

phenyl

H 1-80

phenyl

H 1-81

phenyl

H 1-82

phenyl

H 1-83

phenyl

H 1-84

phenyl

H 1-85

phenyl

H 1-86

phenyl

H 1-87

phenyl

H 1-88

phenyl

H 1-89

phenyl

H 1-90

phenyl

H 1-91

phenyl

H 1-92

phenyl

H 1-93

phenyl

H 1-94

phenyl

H 1-95

phenyl

H 1-96

phenyl

H 1-97

phenyl

H 1-98

phenyl

H 1-99

phenyl

H 1-100

phenyl

H 1-101

phenyl

H 1-102

phenyl

H 1-103

phenyl

H 1-104

phenyl

H 1-105

phenyl

H 1-106

phenyl

H 1-107

phenyl

H 1-108

phenyl

H 1-109

phenyl

H

TABLE 2 R4, R5, R6, Formula R1 R2 R3 X, R7 2-1 phenyl phenyl phenyl H2-2 phenyl phenyl

H 2-3 phenyl phenyl

H 2-4 phenyl phenyl

H 2-5 phenyl phenyl

H 2-6 phenyl phenyl

H 2-7 phenyl phenyl

H 2-8 phenyl phenyl

H 2-9 phenyl phenyl

H 2-10 phenyl phenyl

H 2-11 phenyl phenyl

H 2-12 phenyl

phenyl H 2-13 phenyl

phenyl H 2-14 phenyl

phenyl H 2-15 phenyl

phenyl H 2-16 phenyl

phenyl H 2-17 phenyl

phenyl H 2-18 phenyl

phenyl H 2-19 phenyl

phenyl H 2-20 phenyl

phenyl H 2-21 phenyl

phenyl H 2-22 phenyl

phenyl H 2-23

phenyl

H 2-24

phenyl

H 2-25

phenyl

H 2-26

phenyl

H 2-27

phenyl

H 2-28

phenyl

H 2-29

phenyl

H 2-30

phenyl

H 2-31

phenyl

H 2-32

phenyl

H 2-33

phenyl

H 2-34

phenyl

H 2-35

phenyl

H 2-36

phenyl

H 2-37

phenyl

H 2-38

phenyl

H 2-39

phenyl

H 2-40

phenyl

H 2-41

phenyl

H 2-42

phenyl

H 2-43

phenyl

H 2-44

phenyl

H 2-45

phenyl

H 2-46

phenyl

H 2-47

phenyl

H 2-48

phenyl

H 2-49

phenyl

H 2-50

phenyl

H 2-51

phenyl

H 2-52

phenyl

H 2-53

phenyl

H

TABLE 3 R3, R4, R5, Formula R1 R2 R6 X, R7 3-1 phenyl phenyl phenyl H3-2 phenyl phenyl

H 3-3 phenyl phenyl

H 3-4 phenyl phenyl

H 3-5 phenyl phenyl

H 3-6 phenyl phenyl

H 3-7 phenyl phenyl

H 3-8 phenyl phenyl

H 3-9 phenyl phenyl

H 3-10 phenyl phenyl

H 3-11 phenyl phenyl

H 3-12 phenyl

phenyl H 3-13 phenyl

phenyl H 3-14 phenyl

phenyl H 3-15 phenyl

phenyl H 3-16 phenyl

phenyl H 3-17 phenyl

phenyl H 3-18 phenyl

phenyl H 3-19 phenyl

phenyl H 3-20 phenyl

phenyl H 3-21 phenyl

phenyl H 3-22 phenyl

phenyl H 3-23

phenyl

H 3-24

phenyl

H 2-25

phenyl

H 3-26

phenyl

H 3-27

phenyl

H 3-28

phenyl

H 3-29

phenyl

H 3-30

phenyl

H 3-31

phenyl

H 3-32

phenyl

H 3-33

phenyl

H 3-34

phenyl

H 3-35

phenyl

H 3-36

phenyl

H 3-37

phenyl

H 3-38

phenyl

H 3-39

phenyl

H 3-40

phenyl

H 3-41

phenyl

H 3-42

phenyl

H 3-43

phenyl

H 3-44

phenyl

H 3-45

phenyl

H 3-46

phenyl

H 3-47

phenyl

H 3-48

phenyl

H 3-49

phenyl

H 3-50

phenyl

H 3-51

phenyl

H 3-52

phenyl

H 3-53

phenyl

H

TABLE 4 R3, R5, R6, Formula R1 R2 R4 X, R7 4-1  phenyl phenyl phenyl H4-2  phenyl phenyl

H 4-3  phenyl phenyl

H 4-4  phenyl phenyl

H 4-5  phenyl phenyl

H 4-6  phenyl phenyl

H 4-7  phenyl phenyl

H 4-8  phenyl phenyl

H 4-9  phenyl phenyl

H 4-10 phenyl phenyl

H 4-11 phenyl phenyl

H 4-12 phenyl

phenyl H 4-13 phenyl

phenyl H 4-14 phenyl

phenyl H 4-15 phenyl

phenyl H 4-16 phenyl

phenyl H 4-17 phenyl

phenyl H 4-18 phenyl

phenyl H 4-19 phenyl

phenyl H 4-20 phenyl

phenyl H 4-21 phenyl

phenyl H 4-22 phenyl

phenyl H 4-23

phenyl

H 4-24

phenyl

H 4-25

phenyl

H 4-26

phenyl

H 4-27

phenyl

H 4-28

phenyl

H 4-29

phenyl

H 4-30

phenyl

H 4-31

phenyl

H 4-32

phenyl

H 4-33

phenyl

H 4-34

phenyl

H 4-35

phenyl

H 4-36

phenyl

H 4-37

phenyl

H 4-38

phenyl

H 4-39

phenyl

H 4-40

phenyl

H 4-41

phenyl

H 4-42

phenyl

H 4-43

phenyl

H 4-44

phenyl

H 4-45

phenyl

H 4-46

phenyl

H 4-47

phenyl

H 4-48

phenyl

H 4-49

phenyl

H 4-50

phenyl

H 4-51

phenyl

H 4-52

phenyl

H 4-53

phenyl

H

TABLE 5 R3, R4, R5, Formula R1 R2 X R6, R7 5-1  phenyl phenyl

H 5-2  phenyl phenyl

H 5-3  phenyl phenyl

H 5-4  phenyl phenyl

H 5-5  phenyl phenyl

H 5-6  phenyl phenyl

H 5-7  phenyl phenyl

H 5-8  phenyl phenyl

H 5-9  phenyl phenyl

H 5-10 phenyl phenyl

H 5-11 phenyl

phenyl H 5-12 phenyl

phenyl H 5-13 phenyl

phenyl H 5-14 phenyl

phenyl H 5-15 phenyl

phenyl H 5-16 phenyl

phenyl H 5-17 phenyl

phenyl H 5-18 phenyl

phenyl H 5-19 phenyl

phenyl H 5-20 phenyl

phenyl H 5-21 phenyl

phenyl H 5-22

phenyl

H 5-23

phenyl

H 5-24

phenyl

H 5-25

phenyl

H 5-26

phenyl

H 5-27

phenyl

H 5-28

phenyl

H 5-29

phenyl

H 5-30

phenyl

H 5-31

phenyl

H 5-32

phenyl

H 5-33

phenyl

H 5-34

phenyl

H 5-35

phenyl

H 5-36

phenyl

H 5-37

phenyl

H 5-38

phenyl

H 5-39

phenyl

H 5-40

phenyl

H 5-41

phenyl

H 5-42

phenyl

H 5-43

phenyl

H 5-44

phenyl

H 5-45

phenyl

H 5-46

phenyl

H 5-47

phenyl

H

TABLE 6 R3, R4, R5, Formula R1 R2 R7 R6, X 6-1  phenyl phenyl phenyl H6-2  phenyl phenyl

H 6-3  phenyl phenyl

H 6-4  phenyl phenyl

H 6-5  phenyl phenyl

H 6-6  phenyl phenyl

H 6-7  phenyl phenyl

H 6-8  phenyl phenyl

H 6-9  phenyl phenyl

H 6-10 phenyl phenyl

H 6-11 phenyl phenyl

H 6-12 phenyl

phenyl H 6-13 phenyl

phenyl H 6-14 phenyl

phenyl H 6-15 phenyl

phenyl H 6-16 phenyl

phenyl H 6-17 phenyl

phenyl H 6-18 phenyl

phenyl H 6-19 phenyl

phenyl H 6-20 phenyl

phenyl H 6-21 phenyl

phenyl H 6-22 phenyl

phenyl H 6-23

phenyl

H 6-24

phenyl

H 6-25

phenyl

H 6-26

phenyl

H 6-27

phenyl

H 6-28

phenyl

H 6-29

phenyl

H 6-30

phenyl

H 6-31

phenyl

H 6-32

phenyl

H 6-33

phenyl

H 6-34

phenyl

H 6-35

phenyl

H 6-36

phenyl

H 6-37

phenyl

H 6-38

phenyl

H 6-39

phenyl

H 6-40

phenyl

H 6-41

phenyl

H 6-42

phenyl

H 6-43

phenyl

H 6-44

phenyl

H 6-45

phenyl

H 6-46

phenyl

H 6-47

phenyl

H 6-48

phenyl

H 6-49

phenyl

H 6-50

phenyl

H 6-51

phenyl

H 6-52

phenyl

H 6-53

phenyl

H

In addition, in Formula 1, X and R3 to R7 may be hydrogen.

The compound that is represented by Formula 1 may be manufacturedaccording to the following method. First, the compound A is manufacturedaccording to the method of Journal of Organic Chemistry 2005, 70,3511-3517, and the manufacturing is described below.

The compound B or compound C that is the final target is obtained byconnecting two R1 and R2 functional groups of the synthesized compound Athat is subjected to Suzuki coupling.

A second aspect of the present invention relates to an organicelectronic device which comprises a first electrode, a second electrode,and one or more organic material layers that are disposed between thefirst electrode and the second electrode, wherein one or more layers ofthe organic material layers comprise the compound that is represented byFormula 1.

Herein, the organic material layer may comprise a hole injection layerand a hole transport layer, and the hole injection layer and the holetransport layer may comprise the compound that is represented by Formula1.

In addition, the organic material layer comprises a light emittinglayer, and the light emitting layer comprises the compound of Formula 1.

In addition, the organic material layer comprises an electron transportlayer, and the electron transport layer comprises the compound ofFormula 1.

At this time, it is preferable that the organic electronic device isselected from the group consisting of an organic light emitting device,an organic solar cell, an organic photoconductor (OPC), and an organictransistor.

The compound that is represented by Formula 1 may be formed to theorganic material layer by using a vacuum deposition method and asolution coating method when the organic electronic device ismanufactured. In connection with this, illustrative, but non-limiting,examples of the solution coating process comprise a spin coatingprocess, a dip coating process, an inkjet printing process, a screenprinting process, a spray process, and a roll coating process.

The organic electronic device of the present invention may be producedusing known materials through a known process, modified only in that atleast one layer of organic material layer(s) comprise the compound ofthe present invention, that is, the compound of Formula 1.

The organic material layer of the organic electronic device according tothe present invention may have a single layer structure, or amultilayered structure in which two or more organic material layers arelayered. For example, the organic electronic device according to thepresent invention may have a structure that comprises a hole injectionlayer, a hole transport layer, a light emitting layer, an electrontransport layer, and an electron injection layer as an organic materiallayer. However, the structure of the organic electronic device is notlimited to this, but may comprise a smaller number of organic materiallayers.

Furthermore, the organic electronic device of the present invention maybe produced, for example, by sequentially layering a first electrode,organic material layer(s), and a second electrode on a substrate. Inconnection with this, a physical vapor deposition (PVD) method, such asa sputtering method or an e-beam evaporation method, may be used, butthe method is not limited to these.

As the anode material, in general, it is preferable to use the materialhaving the large work function so as to smoothly perform hole injectioninto the organic material layer. As examples of the anode material thatis capable of being used in the present invention, there are metal oralloy thereof such as vanadium, chrome, copper, zinc, gold and the like;metal oxides such as zinc oxides, indium oxides, indium tin oxides(ITO), indium zinc oxides (IZO) and the like; a combination of metal andoxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound](PEDT),polypyrole and polyaniline, but it is not limited thereto.

As the cathode material, in general, it is preferable to use thematerial having the small work function so as to smoothly performelectron injection into the organic material layer. As detailed examplesof the cathode material, there are metal such as magnesium, calcium,sodium, potassium, titanium, indium, yttrium, lithium, gadolinium,aluminum, silver, tin, and lead or an alloy thereof; a multilayeredstructure material such as LiF/Al or LiO₂/Al, but it is not limitedthereto.

The hole injection material is a material that is capable of wellreceiving holes from the anode at a low voltage, and it is preferablethat the HOMO (highest occupied molecular orbital) of the hole injectionmaterial is a value between the work function of the anode material andthe HOMO of the organic material layer around them. As detailed examplesof the hole injecting material, there are organic materials of metalporphyrin, oligothiophene and arylamine series, organic materials ofhexanitrile hexaazatriphenylene and quinacridone series, organicmaterials of perylene series, and conductive polymers of anthraquinone,polyaniline, and polythiophene series, but they are not limited thereto.

The hole transport material is a material that receives the holes fromthe anode or the hole injection layer and transfer them to the lightemitting layer, and it is preferable to use the material having thelarge mobility to the holes. As detailed examples thereof, there arearylamine-based organic material, a conductive polymer, and a blockcopolymer in which a conjugate portion and a conjugate portion aresimultaneously comprised, but it is not limited thereto.

The light emitting material is a material that receives the holes andthe electrons from the hole transport layer and the electron transportlayer, combines them, such that light at a range of visible rays isemitted, and it is preferable to use the material having excellentphoton efficiency to fluorescence or phosphorescence. As detailedexamples thereof, there are a 8-hydroxy-quinoline aluminum complex(Alq₃); a carbazole-based compound; a dimerized styryl compound; BAlq;10-hydroxybenzoquinoline-metal compound; a benzoxazole, benzthiazole andbenzimidazole-based compound; a poly(p-phenylenevinylene) (PPV)-basedpolymer; a spiro compound; polyfluorene, lubrene, and the like, but itis not limited thereto.

The hole transport material is a material that receives the holes fromthe anode or the hole injection layer and transfer them to the lightemitting layer, and it is preferable to use the material having thelarge mobility to the holes. As detailed examples thereof, there are a8-hydroxyquinoline Al complex; a complex comprising Alq₃; an organicradical compound; a hydroxyflavone metal complex and the like, but it isnot limited thereto.

The organic light emitting device according to the present invention maybe a top emission type, a bottom emission type, or a both-sided emissiontype according to the used material.

The compound according to the present invention may be applied to anorganic electronic device such as an organic solar cell, an organicphotoconductor, an organic transistor and the like by the principle thatis similar to the principle of the organic light emitting device.

MODE FOR INVENTION

The method for manufacturing the compound of Formula 1 and themanufacturing of an organic light emitting device using the same will bedescribed in detail in Preparation Examples and Examples. However, thePreparation Examples and Examples are set forth to illustrate thepresent invention, but the scope of the present invention is not limitedthereto.

PREPARATION EXAMPLE

In general, the compound of Formula 1 according to the present inventioncan be manufactured with multistage chemical reactions. That is, someintermediate compounds are first manufactured, and the compounds ofFormula 1 are manufactured from the intermediate compounds. Theexemplified intermediate compounds are the following compounds. In thecompounds, “Br” may be substituted by any other reactive atom orfunctional group.

Preparation Example 1 Preparation of the Compound S-2

1-bromo-2-(2-phenylethynyl)-benzene (10 g, 38.9 mmol), the compound S-1(10.5 g, 38.9 mmol), and potassium phosphate (K₃PO₄, 24.7 g, 116.5 mmol)were suspended in the mixture of THF (200 mL) and water (200 mL). To thesuspension solution, tetrakis(triphenylphosphine)palladium (898 mg, 1.83mmol) was applied. The mixture was refluxed and agitated for about 24hours, and the refluxed mixture was cooled to room temperature. Theorganic material layer was separated, washed with water, and the aqueouslayer was extracted with chloroform. The organic extract was dried onmagnesium sulfate and concentrated under the vacuum to synthesize thecompound S-2 (10.5 g, yield 84%).

Preparation Example 2 Preparation of the Compound A-1

After the compound S-2 (10.7 g, 33.4 mmol) that was manufactured inPreparation Example 1 was dissolved in CHCl₃ (100 mL), ICl (33.4 mL, 1Msol, 33.4 mmol), slowly dropped, and agitated for 12 hours. The formedsolid was filtered, washed with hexane, and dried to prepare thecompound A-1 (7.02 g, yield 47%).

Preparation Example 3 Preparation of the Compound B-1

The compound A-1 (7.02 g, 15.7 mmol) that was manufactured inPreparation Example 2, phenyl boronic acid (2.30 g, 18.9 mmol), andpotassium phosphate (K₃PO₄, 6.67 g, 31.4 mmol) were suspended in themixture of THF (200 mL) and water (50 mL). To the suspension solution,tetrakis(triphenylphosphine)palladium (363 mg, 0.31 mmol) was applied.The mixture was refluxed and agitated for about 24 hours, and therefluxed mixture was cooled to room temperature. The organic materiallayer was separated, washed with water, and the aqueous layer wasextracted with chloroform. The organic extract was dried on magnesiumsulfate and concentrated under the vacuum to prepare the compound B-1.The B-1 was not purified and used in Preparation Example 4.

Preparation Example 4 Preparation of the Compound C-1

The compound B-1 (6.2 g, 15.6 mmol) that was manufactured in PreparationExample 3, S-3 (5.22 g, 17.3 mmol) and potassium carbonate (6.10 g, 46.9mmol) were suspended in the mixture of THF (100 mL) and water (100 mL).The mixture was maintained for about 24 hours at 50° C. This mixture wascooled to room temperature. The separated organic layer was dried onmagnesium sulfate and concentrated. Thereafter, it was recrystallized onchloroform and methyl alcohol to obtain the compound C-1 (4.85 g, 47%).

Preparation Example 5 Preparation of the Compound 1-18

The compound C-1 (4.85 g, 7.1 mmol) that was manufactured in PreparationExample 4, the compound S-4 (3.98 g, 7.1 mmol), and potassium phosphate(K₃PO₄, 3.0 g, 14.2 mmol) were suspended in the mixture of THF (100 mL)and water (100 mL). To the suspension solution,tetrakis(triphenylphosphine)palladium (165 mg, 0.143 mmol) was applied.The mixture was refluxed and agitated for about 24 hours, and therefluxed mixture was cooled to room temperature. The organic materiallayer was separated, washed with water, and the aqueous layer wasextracted with chloroform. The organic extract was dried on magnesiumsulfate and recrystallized on THF/ethyl acetate to obtain the compound1-18 (4.18 g, 73%).

[M+H]+=809

Preparation Example 6 Preparation of the Compound B-2

The compound A-1 (6.00 g, 13.4 mmol) that was manufactured inPreparation Example 2, naphthalene 2-boronic acid (2.77 g, 16.1 mmol),and potassium phosphate (K₃PO₄, 5.68 g, 26.8 mmol) were suspended in themixture of THF (100 mL) and water (50 mL). To the suspension solution,tetrakis(triphenylphosphine)palladium (309 mg, 0.27 mmol) was applied.The mixture was refluxed and agitated for about 24 hours, and therefluxed mixture was cooled to room temperature. The organic materiallayer was separated, washed with water, and the aqueous layer wasextracted with chloroform. The organic extract was dried on magnesiumsulfate and concentrated under the vacuum to prepare the compound B-2.The B-2 was not purified and used in Preparation Example 7.

Preparation Example 7 Preparation of the Compound C-2

The compound B-2 (5.98 g, 13.4 mmol) that was manufactured inPreparation Example 6, S-3 (4.45 g, 14.7 mmol) and potassium carbonate(3.49 g, 26.8 mmol) were suspended in the mixture of THF (100 mL) andwater (100 mL). The mixture was maintained for about 24 hours at 50° C.This mixture was cooled to room temperature. The separated organic layerwas dried on magnesium sulfate and concentrated. Thereafter, it wasrecrystallized on chloroform and methyl alcohol to obtain the compoundC-2 (5.86 g, 40%).

Preparation Example 8 Preparation of the Compound 1-61

The compound C-2 (5.86 g, 8.0 mmol) that was manufactured in PreparationExample 7, the compound S-5 (3.65 g, 8.0 mmol), and potassium phosphate(K₃PO₄, 3.39 g, 16.0 mmol) were suspended in the mixture of THF (100 mL)and water (100 mL). To the suspension solution,tetrakis(triphenylphosphine)palladium (200 mg, 0.173 mmol) was applied.The mixture was refluxed and agitated for about 24 hours, and therefluxed mixture was cooled to room temperature. The organic materiallayer was separated, washed with water, and the aqueous layer wasextracted with chloroform. The organic extract was dried on magnesiumsulfate and recrystallized on THF/ethyl acetate to obtain the compound1-61 (5.25 g, 86%).

[M+H]+=759

Preparation Example 9 Preparation of the compound 1-6

The compound 1-6 (6.9 g, 91%) was manufactured by using the same methodas Preparation Example 5, except that the compound S-6 (5.1 g, 10.0mmol) was used instead of the compound S-4 in Preparation Example 5.

MS: [M+H]+=759

Preparation Example 10 Preparation of the Compound 1-7

The compound 1-7 (4.8 g, 73%) was manufactured by using the same methodas Preparation Example 5, except that the compound S-7 (4.4 g, 8.7 mmol)was used instead of the compound S-4 in Preparation Example 5.

MS: [M+H]+=759

Preparation Example 11 Preparation of the Compound 1-14

The compound 1-14 (7.3 g, 89%) was manufactured by using the same methodas Preparation Example 5, except that the compound S-8 (4.2 g, 12.0mmol) was used instead of the compound S-4 in Preparation Example 5.

MS: [M+H]+=683

EXAMPLE Examples 1-1

A glass substrate on which a thin film of ITO (indium tin oxide) wascoated to a thickness of 1,500 Å was immersed in distilled water havinga detergent dissolved therein to wash the substrate with ultrasonicwaves. At this time, the detergent as used herein was a productcommercially available from Fisher Co. and the distilled water was onewhich had been twice filtered by using a filter commercially availablefrom Millipore Co. ITO was washed for 30 minutes, and then washing withultrasonic waves was repeated twice for 10 minutes by using distilledwater. After the completion of washing with distilled water, washingwith ultrasonic waves was subsequently carried out by using solventssuch as isopropyl alcohol, acetone and methanol, the resultant productwas dried, and transported to the plasma washing machine. In addition,the substrate was washed by using the oxygen plasma for 5 min, and thesubstrate was transported to the vacuum deposition machine.

On the ITO transparent electrode thus prepared, hexanitrilehexaazatriphenylene was coated to thicknesses of 500 Å by thermal vacuumdeposition to form a hole injecting layer. After NPB (400 Å) that wasthe hole transport material was deposited under the vacuum statethereon, the host compound 1-18 and the dopant D1 compound weredeposited under the vacuum state in a thickness of 300 Å as a lightemitting layer. The electron injection and transport layers were formedby depositing the following E1 compound on the light emitting layerunder the vacuum in a thickness of 200 Å. On the electron injection andtransport layer, lithium fluoride (LiF) in a thickness of 12 Å andaluminum in a thickness of 2,000 Å were subsequently deposited to form acathode. In the above process, the deposition speed of the organicsubstance was maintained at 1 Å/sec, that of lithium fluoride wasmaintained at 0.2 Å/sec, and that of aluminum was maintained at 3 to 7Å/sec. Properties of the manufactured organic light emitting device wereevaluated, and the results are described in the following Table 7.

Examples 1-2 to 1-5

The organic light emitting device was manufactured by using the samemethod as Example 1-1, except that the compounds 1-61, 1-6, 1-7 or 1-14described in the following Table 7 were deposited instead of thecompound 1-18. In the above process, the deposition speed of the organicsubstance was maintained at 1 Å/sec, that of lithium fluoride wasmaintained at 0.2 Å/sec, and that of aluminum was maintained at 3 to 7Å/sec. Properties of the manufactured organic light emitting device wereevaluated, and the results are described in the following Table 7.

Comparative Example 1-1

The organic light emitting device was manufactured by using the samemethod as Example 1-1, except that the following compound H1 was usedinstead of the compound 1-18, properties thereof were evaluated, and theresults thereof are described in the following Table 7.

TABLE 7 [H1]

Driving Current Example Host Dopant voltage efficiency Color coordinate50 mA/cm² material material (V) (cd/A) (x, y) Example 1-1 1-18 D1 7.4022.42 (0.303, 0.655) Example 1-2 1-61 D1 7.79 24.92 (0.314, 0.650)Example 1-3 1-6  D1 7.86 26.74 (0.314, 0.650) Example 1-4 1-7  D1 7.8025.11 (0.314, 0.650) Example 1-5 1-14 D1 8.05 23.06 (0.314, 0.650)Comparative H1 D1 8.22 22.45 (0.314, 0.652) Example 1-1

From the results of Table 7, it can be seen that the organic electronicdevice comprising the compound according to the present invention hasexcellent properties in terms of efficiency, driving voltage, andstability.

Examples 2-1 to 2-3

The organic light emitting device was manufactured by using the samemethod as Example 1-1, except that the compounds 1-6, 1-7 or 1-14described in the following Table 8 were used instead of the compound1-18 as the host material and the following Formula D2 was used as thedopant in Example 1-1.

Comparative Example 2-1

The organic light emitting device was manufactured by using the samemethod as Example 1-1, except that the following Formula H2 was usedinstead of the compound 1-18 as the host material and the followingFormula D2 was used as the dopant in Example 1-1.

TABLE 8 [H2]

[D2]

Driving Current Example Host Dopant voltage efficiency Color coordinate50 mA/cm² material material (V) (cd/A) (x, y) Example 2-1 1-6  D2 6.25.3 (0.134, 0.177) Example 2-2 1-7  D2 6.1 5.6 (0.134, 0.178) Example2-3 1-14 D2 6.3 5.5 (0.134, 0.179) Comparative H2 D2 6.9 5.2 (0.134,0.187) Example 2-1

From the results of Table 8, it can be seen that the organic electronicdevice comprising the compound according to the present invention hasexcellent properties in terms of efficiency, driving voltage, andstability.

1. A compound that is represented by the following Formula 1:

wherein R1 is selected from the group consisting of substituted orunsubstituted C₁˜C₄₀ alkyl group; substituted or unsubstituted C₃˜C₄₀cycloalkyl group; substituted or unsubstituted C₂˜C₄₀ heterocycloalkylgroup; substituted or unsubstituted C₂˜C₄₀ alkenyl group; substituted orunsubstituted C₁˜C₄₀ alkoxy group; substituted or unsubstituted aminogroup; substituted or unsubstituted C₆˜C₄₀ aryl group; substituted orunsubstituted C₃˜C₄₀ heteroaryl group that comprises O, N, or S as aheteroatom; and substituted or unsubstituted C₃˜C₄₀ heteroarylaminegroup that comprises O, N, or S as a heteroatom, R2 is selected from thegroup consisting of substituted or unsubstituted C₁˜C₄₀ alkyl group;substituted or unsubstituted C₃˜C₄₀ cycloalkyl group; substituted orunsubstituted C₃˜C₄₀ heterocycloalkyl group; substituted orunsubstituted C₂˜C₄₀ alkenyl group; substituted or unsubstituted C₁˜C₄₀alkoxy group; substituted or unsubstituted amino group; substituted orunsubstituted C₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀heteroaryl group that comprises O, N, or S as a heteroatom; substitutedor unsubstituted C₅˜C₄₀ arylamine group; and substituted orunsubstituted C₃˜C₄₀ heteroarylamine group that comprises O, N, or S asa heteroatom, R3 to R7 are each independently selected from the groupconsisting of hydrogen; substituted or unsubstituted C₁˜C₄₀ alkyl group;substituted or unsubstituted C₃˜C₄₀ cycloalkyl group; substituted orunsubstituted C₂˜C₄₀ heterocycloalkyl group that comprises O, N, or S asa heteroatom; substituted or unsubstituted C₂˜C₄₀ alkenyl group;substituted or unsubstituted C₁˜C₄₀ alkoxy group; substituted orunsubstituted amino group; substituted or unsubstituted C₆˜C₄₀ arylgroup; substituted or unsubstituted C₃˜C₄₀ heteroaryl group thatcomprises O, N, or S as a heteroatom; substituted or unsubstitutedC₅˜C₄₀ arylamine group; and substituted or unsubstituted C₃˜C₄₀heteroarylamine group that comprises O, N, or S as a heteroatom, and mayform an aliphatic, aromatic, heteroaliphatic or heteroaromaticcondensate ring or a Spiro bond in conjunction with an adjacent group, Xis selected from the group consisting of hydrogen; substituted orunsubstituted C₁˜C₄₀ alkyl group; substituted or unsubstituted C₃˜C₄₀cycloalkyl group; substituted or unsubstituted C₂˜C₄₀ heterocycloalkylgroup that comprises O, N, or S as a heteroatom; substituted orunsubstituted C₂˜C₄₀ alkenyl group; substituted or unsubstituted C₁˜C₄₀alkoxy group; substituted or unsubstituted amino group; substituted orunsubstituted C₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀heteroaryl group that comprises O, N, or S as a heteroatom; andsubstituted or unsubstituted C₃˜C₄₀ heteroarylamine group that comprisesO, N, or S as a heteroatom, and may form an aliphatic, aromatic,heteroaliphatic or heteroaromatic condensate ring or a spiro bond inconjunction with an adjacent group, and all of R3 to R7, and X are nothydrogen.
 2. The compound according to claim 1, wherein in R2 to R7, inthe case of when alkyl group, cycloalkyl group, heterocycloalkyl group,alkenyl group, alkoxy group, amino group, aryl group, heteroaryl group,arylamine group and heteroarylamine group are substituted by the otherfunctional group, they are substituted by one or more groups selectedfrom the group consisting of halogen, deuterium, amino group, nitrilegroup, nitro group, C₁˜C₄₀ alkyl group, C₂˜C₄₀ alkenyl group, C₁˜C₄₀alkoxy group, C₃˜C₄₀ cycloalkyl group, C₂˜C₄₀ heterocycloalkyl groupthat comprises O, N, or S as a heteroatom, C₆˜C₄₀ aryl group and C₃˜C₄₀heteroaryl group that comprises O, N, or S as a heteroatom, and in R1and X, in the case of when alkyl group, cycloalkyl group,heterocycloalkyl group, alkenyl group, alkoxy group, amino group, arylgroup, heteroaryl group and heteroarylamine group are substituted by theother functional group, they are substituted by one or more groups thatare selected from the group consisting of halogen, deuterium, nitrilegroup, nitro group, C₁˜C₄₀ alkyl group, C₂˜C₄₀ alkenyl group, C₁˜C₄₀alkoxy group, C₃˜C₄₀ cycloalkyl group, C₂˜C₄₀ heterocycloalkyl groupthat comprises O, N or S as a heteroatom, C₆˜C₄₀ aryl group and C₃˜C₄₀heteroaryl group that comprises O, N or S as a heteroatom.
 3. Thecompound according to claim 1, wherein R1 is selected from the groupconsisting of substituted or unsubstituted C₆˜C₄₀ aryl group;substituted or unsubstituted C₃˜C₄₀ heteroaryl group that comprises O, Nor S as a heteroatom; and substituted or unsubstituted C₃˜C₄₀heteroarylamine group that comprises O, N or S as a heteroatom, R2 isselected from the group consisting of substituted or unsubstitutedC₆˜C₄₀ aryl group; substituted or unsubstituted C₃˜C₄₀ heteroaryl groupthat comprises O, N or S as a heteroatom; substituted or unsubstitutedC₅˜C₄₀ arylamine group; and substituted or unsubstituted C₃˜C₄₀heteroarylamine group that comprises O, N or S as a heteroatom.
 4. Thecompound according to claim 1, wherein R1 is selected from the groupconsisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ aryl group that is substitutedby C₆˜C₄₀ aryl group or C₃˜C₄₀ heteroaryl group that comprises O, N or Sas a heteroatom; and C₃˜C₂₀ heteroaryl group that is substituted byC₆˜C₂₀ aryl group and comprises O, N or S as a heteroatom, and R2 isselected from the group consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ arylgroup that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀ heteroaryl groupthat comprises O, N or S as a heteroatom or C₅˜C₄₀ arylamine group;C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl group andcomprises O, N or S as a heteroatom; and C₆˜C₂₀ arylamine group.
 5. Thecompound according to claim 1, wherein R1 is selected from the groupconsisting of the substituent groups that are represented by thefollowing Structural Formulas:


6. The compound according to claim 1, wherein R2 is selected from thegroup consisting of the substituent groups that are represented by thefollowing Structural Formulas:


7. The compound according to claim 1, wherein R3 to R7 are hydrogen. 8.The compound according to claim 7, wherein X is selected from the groupconsisting of substituted or unsubstituted C₆˜C₄₀ aryl group;substituted or unsubstituted C₃˜C₄₀ heteroaryl group that comprises O, Nor S as a heteroatom; and substituted or unsubstituted C₃˜C₄₀heteroarylamine group that comprises O, N or S as a heteroatom.
 9. Thecompound according to claim 7, wherein X is selected from the groupconsisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ aryl group that is substitutedby C₆˜C₄₀ aryl group or C₃˜C₄₀ heteroaryl group that comprises O, N or Sas a heteroatom; and C₃˜C₂₀ heteroaryl group that is substituted byC₆˜C₂₀ aryl group and comprises O, N or S as a heteroatom.
 10. Thecompound according to claim 7, wherein X is selected from the groupconsisting of the substituent groups that are represented by thefollowing Structural Formulas:


11. The compound according to claim 1, wherein four of R3 to R7 and Xare hydrogen.
 12. The compound according to claim 11, wherein thesubstituent group except for hydrogen among R3 to R7 is selected fromthe group consisting of substituted or unsubstituted C₆˜C₄₀ aryl group;substituted or unsubstituted C₃˜C₄₀ heteroaryl group that comprises O, Nor S as a heteroatom; substituted or unsubstituted C₅˜C₄₀ arylaminegroup; and substituted or unsubstituted C₃˜C₄₀ heteroarylamine groupthat comprises O, N or S as a heteroatom.
 13. The compound according toclaim 11, wherein the substituent group except for hydrogen among R3 toR7 is selected from the group consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀aryl group that is substituted by C₆˜C₄₀ aryl group, C₃˜C₄₀ heteroarylgroup that comprises O, N or S as a heteroatom or C₅˜C₄₀ arylaminegroup; C₃˜C₂₀ heteroaryl group that is substituted by C₆˜C₂₀ aryl groupand comprises O, N or S as a heteroatom; and C₆˜C₂₀ arylamine group. 14.The compound according to claim 11, wherein the substituent group exceptfor hydrogen among R3 to R7 is selected from the group consisting of thesubstituent groups that are represented by the following StructuralFormulas:


15. The compound according to claim 1, wherein R1 is selected from thegroup consisting of C₆˜C₂₀ aryl group; C₆˜C₂₀ aryl group that issubstituted by C₆˜C₄₀ aryl group or C₃˜C₄₀ heteroaryl group thatcomprises O, N or S as a heteroatom; and C₃˜C₂₀ heteroaryl group that issubstituted by C₆˜C₂₀ aryl group and comprises O, N or S as aheteroatom; R2 is selected from the group consisting of C₆˜C₂₀ arylgroup; C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group,C₃˜C₄₀ heteroaryl group that comprises O, N or S as a heteroatom orC₅˜C₄₀ arylamine group; C₃˜C₂₀ heteroaryl group that is substituted byC₆˜C₂₀ aryl group and comprises O, N or S as a heteroatom; and C₆˜C₂₀arylamine group; R5 is selected from the group consisting of C₆˜C₂₀ arylgroup; C₆˜C₂₀ aryl group that is substituted by C₆˜C₄₀ aryl group,C₃˜C₄₀ heteroaryl group that comprises O, N or S as a heteroatom orC₅˜C₄₀ arylamine group; C₃˜C₂₀ heteroaryl group that is substituted byC₆˜C₂₀ aryl group and comprises O, N or S as a heteroatom; and C₆˜C₂₀arylamine group, and R3, R4, R6, R7 and X are hydrogen.
 16. An organicelectronic device which comprises a first electrode, a second electrode,and one or more organic material layers that are disposed between thefirst electrode and the second electrode, wherein one or more layers ofthe organic material layers comprise the compound according to claim 1.17. The organic electronic device according to claim 16, wherein theorganic material layer comprises at least one layer of a hole injectionlayer and a hole transport layer, and at least one layer comprises thecompound that is represented by Formula
 1. 18. The organic electronicdevice according to claim 16, wherein the organic material layercomprises a light emitting layer, and the light emitting layer comprisesthe compound that is represented by Formula
 1. 19. The organicelectronic device according to claim 16, wherein the organic materiallayer comprises an electron transport layer, and the electron transportlayer comprises the compound that is represented by Formula
 1. 20. Theorganic electronic device according to claim 16, wherein the organicelectronic device is selected from the group consisting of an organiclight emitting device, an organic solar cell, an organic photoconductor(OPC), and an organic transistor.